944263-65-4

Basic information

• Product Name: Demiditraz
• Synonyms: demiditraz;2-[(1S)-1-(2,3-Dimethylphenyl)ethyl]-1H-imidazole;deMiditraz listed;PF 3814927;(S)-2-(1-(2,3-diMethylphenyl)ethyl)-1H-iMidazole;demiditraz:2-((1s)-1-(2,3-dimethylphenyl)ethyl)-1h-IMIDAZOLE
• CAS NO: 944263-65-4
• Molecular Formula: C13H16N2
• Molecular Weight: 200.28
• Mol File: 944263-65-4.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 407.3 °C at 760 mmHg
• Flash Point: 212.2 °C
• Appearance: /
• Density: 1.053
• CAS DataBase Reference: Demiditraz(CAS DataBase Reference)
• NIST Chemistry Reference: Demiditraz(944263-65-4)
• EPA Substance Registry System: Demiditraz(944263-65-4)

Safety Data

• Hazardous Substances Data: 944263-65-4(Hazardous Substances Data)

Usage

General Description

Demitidraz is a powerful organochlorine insecticide and pesticides known for its effectiveness in controlling various pests in agriculture operations. Its chemical name is 4-isopropyl-3,5-dimethyltetrahydro-1,3,5-thiadiazine-2-thione and it belongs to the class of chemicals known as thiadiazines. Demitidraz has a broad spectrum, hence it can be used against several pests and can also work as an acaricide, a substance that kills mites and ticks. Prolonged exposure to this chemical can have serious health impacts including neurotoxicity, therefore it is highly toxic to non-target organisms and has been classified as a possible human carcinogen by the US Environmental Protection Agency.

Synthetic route

demiditraz racemate (944263-08-5) → 2-[(1S)-1-(2,3-dimethylphenyl)ethyl]-1H-imidazole (944263-65-4)

Conditions	Yield
In ethanol Purification / work up;

2-[(1S)-1-(2,3-dimethylphenyl)ethyl]-1H-imidazole (944263-65-4) + methyl iodide (74-88-4) → 2-[(1S)-1-(2,3-Dimethylphenyl)ethyl]-1-methyl-1H-imidazole

Conditions	Yield
With caesium carbonate In acetone at 20℃; for 4h;

phosgene (75-44-5) + 2-[(1S)-1-(2,3-dimethylphenyl)ethyl]-1H-imidazole (944263-65-4) → C14H15ClN2O

Conditions	Yield
With pyridine In dichloromethane; toluene at 0℃; for 0.333333h;

2-[(1S)-1-(2,3-dimethylphenyl)ethyl]-1H-imidazole (944263-65-4) + trichloromethyl chloroformate (503-38-8) → C15H15Cl3N2O2

Conditions	Yield
With pyridine In acetonitrile at 0 - 20℃; for 0.166667 - 0.5h; Product distribution / selectivity;

2-[(1S)-1-(2,3-dimethylphenyl)ethyl]-1H-imidazole (944263-65-4) + benzyl chloroformate (501-53-1) → Benzyl 2-[(1S)-1-(2,3-dimethylphenyl)ethyl]-1H-imidazole-1-carboxylate

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃; for 3h;

2-[(1S)-1-(2,3-dimethylphenyl)ethyl]-1H-imidazole (944263-65-4) + 1,1,1-trifluoro-3-iodopropane (460-37-7) → 2-[(1S)-1-(2,3-Dimethylphenyl)ethyl]-1-(3,3,3-trifluoropropyl)-1H-imidazole

Conditions	Yield
With caesium carbonate In acetonitrile at 100℃; for 0.75h; Microwave irradiation;

2-[(1S)-1-(2,3-dimethylphenyl)ethyl]-1H-imidazole (944263-65-4) + isobutyl chloroformate (543-27-1) → Isobutyl 2-[(1S)-1-(2,3-dimethylphenyl)ethyl]-1H-imidazole-1-carboxylate

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 18h;

2-[(1S)-1-(2,3-dimethylphenyl)ethyl]-1H-imidazole (944263-65-4) + 3-benzyloxybenzyl bromide (1700-31-8) → 1-[3-(Benzyloxy)benzyl]-2-[(1S)-1-(2,3-dimethylphenyl)ethyl]-1H-imidazole

Conditions	Yield
With caesium carbonate In 1-methyl-pyrrolidin-2-one at 20℃; for 48h;

2-[(1S)-1-(2,3-dimethylphenyl)ethyl]-1H-imidazole (944263-65-4) + Chloromethyl pivalate (18997-19-8) → {2-[(1S)-1-(2,3-Dimethylphenyl)ethyl]-1H-imidazol-1-yl}methyl pivalate

Conditions	Yield
With caesium carbonate In acetone at 20℃; for 18h;

1-(4-(bromomethyl)phenyl)-1H-1,2,4-triazole + 2-[(1S)-1-(2,3-dimethylphenyl)ethyl]-1H-imidazole (944263-65-4) → 1-[4-({2-[(1S)-1-(2,3-Dimethylphenyl)ethyl]-1H-imidazol-1-yl}methyl)phenyl]-1H-1,2,4-triazole

Conditions	Yield
With caesium carbonate In 1-methyl-pyrrolidin-2-one at 20℃; for 18h;

Upstream product

• 944263-08-5 demiditraz racemate 

Relevant articles and documents

SUBSTITUTED IMIDAZOLE COMBINATIONS

This invention relates to a composition comprising a combination of a) an alpha substituted 2-benzyl substituted imidazole and b) a 1-N-arylpyrazole, and optionally c) an insect growth regulator, and their use as a parasiticide in mammals.